Use in cosmetics of lipophilic derivatives of amino deoxyalditols, cosmetic compositions containing them, and novel alkyl carbamates

ABSTRACT

The invention is characterized by the use in cosmetic compositions of one or more lipophilic derivatives of amino deoxyalditols corresponding to the general formula: ##STR1## in which: R 1  is a saturated linear C 14  -C 40  aliphatic radical; 
     R 2  is a hydrogen atom or a linear C 1  -C 6  alkyl radical; 
     X is an oxygen atom or a methylene radical; and 
     n is an integer from 1 to 5; 
     with the proviso that when X is a methylene radical R 1  contains from 19 to 39 carbon atoms. 
     Application to the preparation of cosmetic compositions for the treatment of keratinous substances and for buccodental hygiene.

This is a division of Application Ser. No. 08/356,269, filed as PCT/FR94/00402 Apr. 11, 1994.

The subject of the present invention is the use in cosmetics of lipophilic derivatives of amino deoxyalditols, and cosmetic compositions containing one or more of these derivatives.

It is known that mammalian hairs contain a certain number of lipid compounds the structure and distribution of which are not yet fully defined. Along with apolar lipids secreted by the sebaceous glands and for a long time considered to be the only lipids present on the hairs, the presence of other, polar lipids has been demonstrated; among these are cholesterol sulfate, fatty acids and fatty alcohols. These polar compounds have long evaded the investigations of researchers, probably due to their very low solubility in the usual extraction solvents, based on chloroform, methanol and hexane. Their extraction is so difficult that it is even suspected by some that (for some of them) they are covalently bonded to the cell surfaces (P. W. WERTZ. Lipids 23 No. 9 (1988) 878-881).

In man, frequent washing, wear, climatic aggressions and certain cosmetic treatments to which the hair, the eyelashes and the beard are subjected are responsible for the decrease in the esthetic properties of the hairs in general.

It was thus seen to be necessary in the cosmetics field, and in particular for compositions for treating the hair, to repair the damage suffered by the provision of polar lipid products which, on account of their very low solubility in water, will not be removed during washing, even more so since their strong polarity will allow them to become associated with the very structure of the hair, this case not being possible with weakly polar or non-polar compounds of waxy type which are often recommended for improving the condition of the hair.

Certain compounds obtained by extraction from animal or plant tissues have already been recommended for this type of application. In particular, products such as ceramides have been described in the document EP-A-278 505. However, the difficulty in obtaining them in industrial amounts with a sufficient degree of purity makes the use of these compounds unattractive.

Document WO 92/05764 describes shampoo compositions containing at least 1% by weight of a surface-active agent chosen from polyhydroxylated fatty acid amides corresponding to the formula: ##STR2## in which R¹ represents hydrogen, a C₁ -C₄ carbon/hydrogen-based radical, 2-hydroxyethyl, 2-hydroxypropyl or mixtures thereof, and preferably the methyl radical; R² is a C₅ -C₃₁ carbon/hydrogen-based residue, preferably a C₇ -C₁₉ straight-chain alkyl or alkenyl, even better a C₉ -C₁₇ straight-chain alkyl or alkenyl, and most particularly a C₁₁ -C₁₅ straight-chain alkyl or alkenyl, or mixtures thereof; and Z is a polyhydroxylated carbon-based residue having a linear carbon/hydrogen-based chain with at least 3 hydroxyls attached to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) of the latter. The polyhydroxylated fatty acid amides used as surface-active agents in the shampoo compositions of document WO 92/05764 must, on account of their detergent properties, have an acceptable solubility in water, and it is consequently recommended to use polyhydroxylated fatty acid amides having C₁₂ -C₁₈ R² substituents, which give materials having the best compromise between the ease of manufacture, the solubility in water and the detergent activity.

It was thus seen to be necessary to search for fully defined synthetic compounds which are solid at the temperatures of use, in order to restructure the hairs without giving them an undesirable oily appearance, and which furthermore are insoluble in water alone but may be placed on the hair using a formula which is essentially aqueous. After being placed on the hair, these compounds will have to provide excellent properties thereto, such as untangling, shine, liveliness and pleasant feel.

The Applicant has found that compounds corresponding particularly well to the above set of criteria were lipophilic derivatives of amino deoxyalditols and more particularly nonionic compounds of linear polyol type combined with a long fatty chain, the two sequences of these amphiphilic compounds being linked by functional groups which are themselves highly polar, of amide or carbamate type.

Furthermore, these compounds proved to be advantageous in the formulation of compositions for buccodental and body hygiene.

Consequently, one subject of the present invention is the use of the above derivatives in cosmetic compositions.

The subject of the invention is also the cosmetic compositions containing such compounds, as well as their application for treating keratinous substances such as the skin or the hair, and for buccodental hygiene.

The subject of the invention is also novel lipophilic derivatives of amino deoxyalditols, of carbamate type, which may be used in the compositions according to the invention.

Other subjects of the invention will become apparent on reading the description and the examples which follow.

The lipophilic derivatives of amino deoxyalditols used in accordance with the invention in cosmetic compositions, in particular for treating the skin, the hair or for buccodental hygiene, are characterized in that they correspond to the general formula: ##STR3## in which R¹ is a saturated linear C₁₄ -C₄₀ aliphatic radical;

R² is a hydrogen atom or a linear C₁ -C₆ alkyl radical;

X is an oxygen atom or a methylene radical; and

n is an integer from 1 to 5, with the proviso that when X is a methylene radical R¹ is a saturated linear C₁₉ -C₃₉ aliphatic radical.

Some of the compounds corresponding to the general formula (I) above are known. In particular, U.S. Pat. Nos. 1,985,424 and 2,703,798 describe amides corresponding to this general formula. However, the only compounds described correspond to short or medium-length lipophilic chains limited to 18 carbon atoms.

U.S. Pat. No. 2,040,997 describes carbamates corresponding to the formula (I) above. These carbamates correspond to the general formula ##STR4## in which R is an aliphatic radical containing polyhydroxy substitutions, X is a hydrogen atom or an alkyl radical and A is an aliphatic hydrocarbon radical having 8 or more carbon atoms. A preferably represents a straight-chain alkyl group having 10 to 20 carbon atoms. The carbamates used as synthetic intermediates are illustrated only by the sole dodecyl compound.

In the formula (I) above, and when X represents an oxygen atom, R¹ represents a saturated linear C₁₄ -C₄₀, preferably a C₁₄ -C₃₂ and even better a C₁₆ -C₂₂, aliphatic radical. When X represents a methylene radical, R¹ represents a saturated linear C₁₉ -C₃₉, preferably a C₂₁ -C₂₉, aliphatic radical; R² represents a hydrogen atom or a linear C₁ to C₆ alkyl radical, preferably methyl; and n is an integer from 1 to 5 and preferably equal to 4.

Among the recommended derivatives of formula (I) there may be mentioned

1-[docosanoyl-methyl-amino]-1-deoxy-D-glucitol,

[hexadecyloxycarbonyl-methyl-amino]-1-deoxy-D-glucitol,

1-[octadecyloxycarbonyl-methyl-amino]-1-deoxy-D-glucitol,

1-[docosyloxycarbonyl-methyl-amino]-1-deoxy-D-glucitol, and

1-[tetracosanoyl-methyl-amino]-1-deoxy-D-glucitol.

There may also be mentioned the amides derived from mixtures of fatty acids or the carbamates derived from a mixture of fatty alcohols; fatty alcohols or acids may be obtained by synthesis or by extraction from natural, plant or animal waxes.

As an example, octacosanol extracted from rice seeds or from wheat and sold by the company NIPPON OILS is a mixture of C₂₆ -C₃₆ alcohols. Mixtures of C₂₂ - and C₂₄ -rich acids may be obtained, inter alia, from rice wax, carnauba wax or beeswax.

The processes for preparing the derivatives of formula (I) above are well known to those skilled in the art. It is possible, for example, to prepare the amides corresponding to the formula (I) by the method described by E. K. Hildreth, Biochem J. 207 (1982) 363.

According to this method, a mixed anhydride is prepared in a first phase by reacting an acid of formula R¹ COOH, where R¹ is defined as above, with a lower alkyl haloformate, preferably an ethyl haloformate, in a suitable solvent in the presence of a base, for example pyridine, in order to form a mixed anhydride solution.

In a second phase, the mixed anhydride solution obtained is reacted with an N-alkylamine of formula: ##STR5## where R² and n are defined as above, in a suitable solvent, for example alkanols such as methanol or ethanol, or alternatively dimethylformamide.

The carbamates corresponding to the formula (I) may be prepared by reacting an amine of formula ##STR6## where R² and n are defined as above, with a suitable C₁₄ -C₄₀ alkyl haloformate, for example a chloroformate, in the presence of sodium hydrogen carbonate, water and a suitable solvent, for example tetrahydrofuran.

The present invention also relates to novel carbamates falling within the scope of the general formula (I) above. More particularly, these novel carbamates correspond to the general formula (II) ##STR7## in which R³ is a saturated linear C₂₂ -C₄₀, preferably a C₂₂ -C₂₆, aliphatic radical, R⁴ is a hydrogen atom or a linear C₁ -C₆ alkyl radical and m is an integer from 1 to 5, preferably equal to 4. Preferably, R³ is the docosyl radical and R⁴ is a methyl radical.

Cosmetic compositions, in particular the compositions for treating the hair and the skin and for buccodental hygiene, in accordance with the invention, are characterized in that they contain at least one derivative corresponding to the formula (I) above in a cosmetically acceptable support.

When the compositions according to the invention are used for treating the hair, an improvement in the untangling of wet hair and the provision of softness and smoothness to dried hair are observed.

Generally, the compound or compounds of formula (I) are present in the composition at a concentration between 0.01 and 15% by weight relative to the total weight of the composition, and preferably at a concentration of 0.1 to 10% by weight relative to the total weight of the composition.

The cosmetically acceptable support may consist of a fatty phase or of an aqueous medium which consists solely of water or of a mixture of water and a cosmetically acceptable solvent, such as a C₁ -C₄ lower alkyl, for instance ethanol, isopropanol or n-butanol; alkylene glycols, for instance ethylene glycol; glycol ethers.

The compositions according to the invention may be provided in the form of an emulsion (a milk, cream or an ointment), a vesicle dispersion, a solid stick, an aqueous solution or dispersions which are optionally thickened or gelled, aerosol foams or spray.

The compositions may additionally contain surface-active agents which are well known in the state of the art, such as anionic, nonionic, cationic, amphoteric or zwitterionic surface-active agents or mixtures thereof.

The compositions are, for example, emollient lotions, milks or creams, milks or creams for skin care or for hair care, creams, lotions or milks for removing make-up, foundation bases, antisun lotions, milks or creams, lotions, milks or creams for artificial tanning, shaving creams or foams, after-shave lotions, shampoos, conditioners or mascaras.

These compositions may also be provided in the form of sticks for the lips, intended either to color them or to prevent chapping, or in the form of make-up products for the eyes or powders and foundations for the face.

When the compositions according to the invention are provided in the form of emulsions of the water-in-oil type or oil-in-water type, the fatty phase consists essentially of a mixture of compound of formula (I) with at least one oil, and optionally another fatty substance.

The fatty phase of the emulsions may constitute 5 to 60% of the total weight of the emulsion.

The aqueous phase of the said emulsions preferably constitutes 30 to 85% of the total weight of the emulsion.

The proportion of the emulsifying agent may be between 1 and 20%, and preferably between 2 and 12%, of the total weight of the emulsion.

When the compositions according to the invention are provided in the form of oily, oleo-alcoholic or aqueous-alcoholic lotions, they may consist of, for example, antisun lotions containing a screening agent for absorbing UV rays, or of emollient solutions for the skin; the oily lotions may also consist of foaming oils containing an oleo-soluble surfactant, or of bath oils, etc.

Among the main adjuvants which may be present in the compositions according to the invention, there may be mentioned fatty substances such as mineral, animal or plant oils or waxes, fatty acids, fatty acid esters such as fatty acid triglycerides which have from 6 to 18 carbon atoms, or fatty alcohols; emulsifying agents such as oxyethylenated fatty alcohols or polyglycerol alkyl ethers, solvents such as lower monoalcohols or polyalcobols containing from 1 to 6 carbon atoms, or alternatively water.

The mono- or polyalcohols which are more particularly preferred are chosen from ethanol, isopropanol, propylene glycol, glycerol and sorbitol.

By way of fatty substances, among the mineral oils there may be mentioned liquid paraffin; among the animal oils there may be mentioned whale oil, seal oil, menhaden oil, halibut liver oil, cod oil, tuna oil, tortoise oil, ox foot oil, horse foot oil, sheep foot oil, mink oil, otter oil, marmot oil, etc.; among the plant oils there may be mentioned almond oil, wheatgerm oil, olive oil, corn germ oil, jojoba oil, sesame oil, sunflower oil, palm oil, walnut oil, karite oil, shorea oil, macadamia oil, blackcurrant seed oil and the like.

Among the fatty acid esters, it is possible to use the saturated or unsaturated C₁₂ to C₂₂ acid esters of lower alcohols such as isopropanol or glycerol or of saturated or unsaturated, linear or branched C₈ to C₂₂ fatty alcohols or alternatively of C₁₀ -C₂₂ 1,2-alkanediols.

As fatty substances, there may also be mentioned petrolatum, paraffin, lanolin, hydrogenated lanolin, tallow, acetylated lanolin and silicone oils.

Among the waxes, there may be mentioned Sipol wax, lanolin wax, beeswax, candelila [sic] wax, microcrystalline wax, carnauba wax, spermaceti, cocoa butter, karite butter, silicone waxes, hydrogenated oils which are solid at 25° C., sucroglycerides, and the oleates, myristates, linoleates and stearates of Ca, Mg and Al.

Among the fatty alcohols, there may be mentioned lauryl alcohol, cetyl alcohol, myristyl alcohol, stearyl alcohol, palmityl alcohol and oleyl alcohol and GUERBET alcohols such as 2-octyldodecanol, 2-decyltetradecanol or 2-hexyldecanol.

By way of emulsifying agents, among the polyoxyethylenated fatty alcohols there may be mentioned lauryl alcohol, cetyl alcohol, stearyl alcohol and oleyl alcohol containing from 2 to 20 moles of ethylene oxide, and among the polyglycerol alkyl ethers there may be mentioned the C₁₂ -C₁₈ alcohols containing from 2 to 10 moles of glycerol.

It may also be useful to use thickening agents such as cellulose derivatives, polyacrylic acid derivatives, guar gum, carob gum or xanthan gum.

The compositions in accordance with the invention may be provided in the form of a vesicle dispersion of ionic or nonionic amphiphilic lipids. They are especially prepared by swelling the lipids in an aqueous solution in order to form spherules which are dispersed in the aqueous medium, as described in the article BANGHAM, STANDISH & WATKINS, J. Mol. Biol., 13,238 (1965) or in the patents FR-2,315,991 and 2,416,008 of the Applicant.

The various types of preparation processes are described in "Les liposomes en biologie cellulaire et pharmacologie" [Liposomes in cell biology and pharmacology], Edition INSERM/John Liberty Eurotext, 1987, pages 6 to 18.

The composition according to the invention may also contain adjuvants commonly used in cosmetics and especially moisturizing products, emollients, products for treating skin complaints, sunscreen agents, germicides, dyes, preserving agents, fragrances and propellants, and sequestering agents.

The examples which follow are intended to illustrate the invention, without any limitation being implied thereby.

PREPARATION EXAMPLES Example 1 Preparation of 1-[docosanoyl-methyl-amino]-1-deoxy-D-glucitol

Phase A: Preparation of the mixed anhydride

140 ml of tetrahydrofuran and 23.4 g of ethyl chloroformate are introduced into a reactor, a solution of 70 g of behenic acid sold under the name "PRIFRAC 2989" by the company UNICHEMA dissolved in 140 ml of tetrahydrofuran is added steadily at 40° C., followed by neutralization with 21.8 g of triethylamine, and the solution is filtered, which solution will be used as it is in phase B.

Phase B:

40.1 g of N-methylglucamine are dissolved, at 60° C., in 400 ml of dimethylformamide in a reactor, followed by slow addition of the mixed anhydride obtained in phase A, and the reaction is continued at 60° C. for 3 hours.

At the end of the reaction, the reaction mixture is diluted with 400 ml of water and is cooled to 40° C. After draining the crystallized product, it is recrystallized from 1 l of 95° ethanol. 94.6 g of a white product are obtained, equivalent to a final yield of 88%.

ANALYSES

    ______________________________________                                         Elemental analysis:                                                                       % C  % H        % N    % O                                          ______________________________________                                         Theoretical  67.27  11.49      2.71 18.54                                      Found        67.44  11.36      2.75 18.43                                      ______________________________________                                    

Melting point: 114° C.

Example 2 Preparation of 1-[hexadecyloxycarbonyl-methyl-amino]-1-deoxy-D-glucitol

11.7 g of N-methylglucamine are dissolved in a mixture of 30 ml of water and 40 ml of tetrahydrofuran in a reactor, followed by addition and dispersion of 20 g of sodium hydrogen carbonate.

While maintaining the temperature of the reaction mixture at 20° C., 18.3 g of hexadecyl chloroformate marketed by S.N.P.E. are added dropwise, and the mixture is then left to react for two hours and is diluted with 100 ml of tetrahydrofuran.

The reaction mixture is filtered; the solid product recovered is dissolved in 500 ml of acetone; the insoluble fraction is removed by hot filtration.

After cooling at 1° C. for 12 hours, the crystallized product is recovered and dried. 15.5 g of a pure white product are obtained, equivalent to a final yield of 56%.

ANALYSES

    ______________________________________                                         Elemental analysis                                                                        % C  % H        % N    % O                                          ______________________________________                                         Theoretical  62.17  10.65      3.02 24.16                                      Found        62.13  10.67      3.13 24.16                                      ______________________________________                                    

Melting point: 80° C.

Example 3 Preparation of 1-[octadecyloxycarbonyl-methyl-amino]-1-deoxy-glucitol

The experimental procedure of Example 2 is repeated, replacing the hexadecyl chloroformate with octadecyl chloroformate. The expected product obtained is white and the final yield is 66%.

ANALYSES

    ______________________________________                                         Elemental analysis                                                                        % C  % H        % N    % O                                          ______________________________________                                         Theoretical  63.51  10.86      2.85 22.78                                      Found        63.57  10.94      2.94 22.88                                      ______________________________________                                    

Melting point: 85° C.

Example 4 Preparation of 1-[docosyl-oxycarbonyl-methyl-amino]-1-deoxy-D-glucitol

70.2 g of N-methylglucamine are dissolved in a mixture of 180 ml of water and 240 ml of tetrahydrofuran in a reactor, followed by addition and dispersion of 12 g of sodium hydrogen carbonate.

While maintaining the temperature of the reaction mixture at 5° C., 140.1 g of docosyl chloroformate dissolved in 100 ml of tetrahydrofuran are added dropwise over two hours; the reaction mixture is diluted with a further 1 l of tetrahydrofuran and is left to react for two hours.

The reaction mixture is filtered; after separation of the phases once settling has taken place, the organic phase is collected and concentrated, and the residue is then recrystallized from one liter of a mixture of 8 volumes of acetone and 2 volumes of methanol. 70 g of a pure white product are obtained, equivalent to a final yield of 36%.

ANALYSES

    ______________________________________                                         Elemental analysis                                                                       % C        % H    % N                                                ______________________________________                                         Theoretical 63.71        10.93  3.23                                           Found       63.83        10.91  3.22                                           ______________________________________                                    

Melting point: 94.6° C.

Example 5 Preparation of 1-[Docosanoylamino]-1-deoxy-D-glucitol

The experimental procedure of Example 1 is repeated, replacing the N-methylglucamine with 37.2 g of glucamine; 59 g of the expected product are obtained (Y=57%), by recrystallization from propanol.

    ______________________________________                                         ELEMENTAL ANALYSIS:                                                                       % C  % H        % N    % O                                          ______________________________________                                         Theoretical  66.76  11.4       2.78 19.06                                      Found        66.7   11.4       2.58 18.92                                      ______________________________________                                    

Melting point: 136° C.

The examples which follow are intended to illustrate the cosmetic formulations according to the present invention.

Example 6 Preparation of 1-[tetracosanoyl-methyl-amino]-1-deoxy-D-glucitol

Phase A: preparation of the mixed anhydride

1.55 g of ethyl chloroformate dissolved in 10 ml of tetrahydrofuran are introduced into a reactor.

At 0° C., a solution of 5 g of tetracosanoic acid sold under the name "NAFOL 24/26 Acid" by the company CONDEA and of composition:

C₂₀ : 5%,

C₂₂ : 5%,

C₂₄ : 60%,

C₂₆ : 22%,

C₂₈ : 4%,

in 50 ml of tetrahydrofuran which has been salified beforehand with 1.44 g of triethylamine, is introduced slowly. The solution is allowed to react for 2 hours and is then filtered, which solution will be used as it is in phase B.

Phase B:

2.6 g of N-methylglucamine are dissolved, at 80° C., in 50 ml of dimethylformamide in a reactor and the temperature is maintained at 60° C.; the mixed anhydride obtained in phase A is then added slowly and the reaction is continued at 60° C. for 3 hours.

The mixture is cooled to 4° C. and is left to crystallize for 1 hour; after filtration, the solid is recrystallized from methanol.

3.2 g of the expected product are thus obtained (Y=43%)

    ______________________________________                                         ELEMENTAL ANALYSIS:                                                                       % C  % H        % N    % O                                          ______________________________________                                         Theoretical  68.21  11.63      2.57 17.59                                      Found        68.28  11.69      2.45 17.59                                      ______________________________________                                    

Melting point: 102° C.

The mass spectrum is in accordance with the expected structure.

    ______________________________________                                         Example A: Shampoo                                                             Compound of Example 1      5      g                                            Alkyl (C.sub.9 /C.sub.10 /C.sub.11 - 20/40/40) (1,4)                                                      15     g AS                                         polyglucoside sold by the company HENKEL                                       at a concentration of 500 g % [sic] of                                         active substance                                                               Preserving agent qs                                                            Fragrance qs                                                                   Dye qs                                                                         Water qs                   100    g                                            pH adjusted to 7 with hydrochloric acid                                        A thickened milky liquid is obtained.                                          EXAMPLE B: Shampoo                                                             Compound of Example 1      0.1    g                                            Sodium lauryl ether sulfate (C.sub.12 /C.sub.14 -                                                         15     g AS                                         70/30) 2.2 mol EO sold under the name                                          "EMPICOL ESB/3 FL" by the company                                              MARCHON at a concentration of 28% of active                                    substance                                                                      Cocoyl betaine in aqueous solution at a                                                                   2.5    g AS                                         concentration of 32%                                                           Coconut acid monoisopropanolamide sold                                                                    1      g                                            under the name "EMPILAN CIS" by the                                            company MARCHON                                                                Cetyl 2-hydroxycetyl-stearyl ether/cetyl                                                                  2.5    g                                            alcohol                                                                        Fragrance qs                                                                   Preserving agent qs                                                            Dyes qs                                                                        Water qs                   100    g                                            pH adjusted to 6.7 with triethanolamine.                                       A thickened milky liquid is obtained.                                          EXAMPLE C: Shampoo                                                             Compound of Example 1      1.5    g                                            Polyglycerolated dodecanediol containing                                                                  10     g AS                                         3.5 mol of glycerol                                                            Hexanedecanediol ether (3 mol) and                                                                        2.5    g                                            polyethylene glycol ether (60 EO)                                              Preserving agent qs                                                            Fragrance qs                                                                   Dyes qs                                                                        Water qs                   100    g                                            pH adjusted to 7.6 with triethanolamine                                        A thick clear liquid is obtained                                               EXAMPLE D: Shower gel                                                          Compound of Example 1      0.5    g                                            Lauric acid (C.sub.12 /C.sub.14 - 70/30) carboxyl                                                         10     g AS                                         ether 4.5 EO sold under the name "AKYPO RLM                                    45" at a concentration of 90 g % of active                                     substance by the company RIOIIN                                                Sodium cocoamidoethyl (N-hydroxyethyl,                                                                    5      g AS                                         N-carboxymethyl)glycinate                                                      Sodium lauroyl sarcosinate sold under the                                                                 8      g AS                                         name "ORAMIX L 30" by the company SEPPIC                                       at a concentration of 30 g % AS                                                Dioleate of polyethylene glycol (55 EO)                                                                   2      g AS                                         and of propylene glycol/water (40/40/20)                                       sold under the name "ANTIL 141" liquid by                                      the company GOLDSCHMIDT at a concentration                                     of 40 g % AS                                                                   Preserving agent qs                                                            Fragrance qs                                                                   Dye qs                                                                         Water qs                   100    g                                            pH adjusted to 7.% with hydrochloric acid.                                     A clear fluid gel is obtained.                                                 EXAMPLE E: Conditioner                                                         Compound of Example 1      2      g                                            Distearyldimethylammonium chloride                                                                        2      g                                            Hydroxyethylcellulose sold under the name                                                                 1      g                                            "NATROSOL 250 HHR" by the company                                              AQUALON                                                                        Preserving agent qs                                                            Fragrance qs                                                                   Dye qs                                                                         Water qs                   100    g                                            pH adjusted to 4.5 with triethanolamine.                                       A white fluid gel is obtained.                                                 EXAMPLE F: Conditioner                                                         Compound of Example 1      10     g                                            Distearyldimethylammonium chloride                                                                        5      g                                            Mixture of cetylstearyl alcohol and                                                                       3      g                                            oxyethylenated cetylstearyl alcohol                                            containing 33 EO (80/20)                                                       Cetyl alcohol              1      g                                            Stearyl alcohol            1      g                                            Preserving agent qs                                                            Fragrance qs                                                                   Dye qs                                                                         Water qs                   100    g                                            pH adjusted to 4 with triethanolamine.                                         A thick white cream is obtained.                                               EXAMPLE G: After-sun care -                                                    oil-in-water emulsion                                                          1-[Docosanoyl-methyl-amino]-1-deoxy-D-                                                                    0.5    g                                            glucitol (compound of Example 1)                                               Glycerine                  3      g                                            Sodium hydroxide           0.24   g                                            Cetyl alcohol              2.5    g                                            Ethylenediaminetetraacetic acid (EDTA)                                                                    0.1    g                                            Stearyl alcohol            1      g                                            Sorbitol                   3      g                                            Sunflower oil              6      g                                            Polyoxyethylenated sorbitan monolaurate                                                                   2      g                                            containing 20 mol of ethylene oxide, sold                                      under the name "TWEEN 20" by the                                               company ICI                                                                    Crosslinked polyacrylic acid sold under the                                                               0.3    g                                            name "CARBOPOL 941" by the company                                             GOODRICH                                                                       Oily extract of yolk       2      g                                            Silicone oil sold under the name "SILBIONE                                                                0.15   g                                            ANTIMOUSSE [ANTI-FOAM] 70 452" by the                                          company RHONE POULENC                                                          Beeswax                    1      g                                            Oat flour                  0.5    g                                            Karite butter              1.5    g                                            Preserving agents, antioxidant, fragrance qs                                   Water qs                   100    g                                            ______________________________________                                    

The emulsion is prepared according to the following experimental procedure:

1) Swell "CARBOPOL 941" with glycerine in some water, neutralize to pH 7 with sodium hydroxide at 60° C. with stirring (Phase 1)

2) Add the emulsifying agents TWEEN 20 and oily extract of yolk, and the oat flour to phase 1 (Phase 2)

3) Dissolve EDTA in some water at 60° C.

Add the sorbitol, the karite butter and the beeswax and the silicone oil, with stirring at 60° C.

Leave to stir for 30 minutes (Phase 3)

4) Add phase 2 to phase 3 at 60° C. with stirring (Phase 4)

5) Melt the sunflower oil, the cetyl alcohol and stearyl alcohol co-emulsifying agents, the preserving agents for the fatty phase and compound of Example 1, at 70° C. (Phase 5).

6) Mix phases 4 and 5 with stirring.

7) Allow to cool to 40° C.

Add the preserving agents for the aqueous phase and the fragrance. Continue to stir until completely cooled.

    ______________________________________                                         EXAMPLE H: Direct dyeing                                                       ______________________________________                                         Compound of Example 2      0.1    g                                            Propylene glycol monomethyl ether                                                                         10     g                                            Oxyethylenated nonylphenol (9 EO) marketed                                                                8      g                                            under the name "RHODIASURF NP 9 OR" by                                         the company RHONE POULENC                                                      Coconut diethanolamide was [sic] sold under                                                               2      g                                            the name "COMPERLAN KD" by the company                                         HENKEL                                                                         N1,N4,N4-tris(β-hydroxyethyl)-1,4-diamino-                                                           0.5    g                                            2-nitrobenzene                                                                 1-Amino-2-nitro-4-B-hydroxyethylamino-                                                                    0.05   g                                            benzene [sic]                                                                  pH agent qs                pH     9                                            Demineralized water qs     100    g                                            ______________________________________                                    

Mode of application:

The locks of permanent-waved gray hair containing 90% of white hairs are immersed in the dye composition, in a proportion of 20 g of formula per 3 g of hair. The formula is allowed to act for 30 minutes. The hair is then rinsed and dried. The hair is dyed violet.

    ______________________________________                                         EXAMPLE I:                                                                     Alkaline oxidation dye - cream support                                         ______________________________________                                         Compound of Example 1    0.3    g                                              Cetylstearyl alcohol (C.sub.16 /C.sub.18 50/50) sold                                                    18     g                                              under the name CIRE DE LANETTE O by the                                        company HENKEL                                                                 2-octyldodecanol         3      g                                              Oxyethylenated cetylstearyl alcohol                                                                     3      g                                              (C.sub.16 /C.sub.18 35/65) (15 EO) sold under the name                         "MERGITAL CS 15" by the company                                                SINNOVA-HENKEL                                                                 Ammonium laury sulfate at a concentration                                                               12     g as such                                      of 30% AS                                                                      Polymer of formula                                                              ##STR8##                2Cl.sup.-                                             in aqueous solution at a concentration of 60%                                                           3      g as such                                      of active substance, sold under the name                                       "MEXOMER PO" by the company CHIMEX                                             Ammonium thiolactate (at a concentration                                                                0.8    g                                              of 50% of thiolactic acid equivalent)                                          Aqueous ammonia at a concentration of                                                                   12     g                                              20% of NH3                                                                     Para-aminophenol         0.436  g                                              1-Methyl-2-hydroxy-4-β-hydroxyethylamino-                                                          0.668  g                                              benzene                                                                        Demineralized water  qs  100    g                                              ______________________________________                                    

Mode of application

The composition obtained is diluted at the time of use with 1.5 times its weight of 20 volume hydrogen peroxide, the pH of which is 3.

The mixture thus prepared is applied to gray hair containing 90% of white hairs, which hair may or may not have been permanent-waved, in a proportion of 28 g per 3 g of hair. The mixture is allowed to act for 30 minutes.

The hair is then rinsed, washed with a shampoo and rinsed. The hair is dyed a coppery color or an intense coppery color depending on whether this is natural or permanent-waved hair respectively.

    ______________________________________                                         EXAMPLE J: Anti-sun oil-in-water emulsion                                      Compound of Example 2      2      g                                            Stearic acid               2      g                                            Stearyl alcohol            1      g                                            Liquid paraffin            10     g                                            2-Ethylhexyl para-methoxycinnamate sold                                                                   5      g                                            under the name "PARSOL MCX" by the                                             company GIVAUDAN                                                               Glycerine                  3      g                                            Sorbitol                   2      g                                            Acrylic acid/C.sub.10 -C.sub.30 alkyl acrylate                                                            0.3    g                                            crosslinked copolymer sold under the name                                      "PEMULEN TR-1" by the company                                                  GOODRICH                                                                       Triethanolamine            0.4    g                                            Preserving agents qs                                                           Water qs                   100    g                                            EXAMPLE K: Anti-sun oil-in-water emulsion                                      Compound of Example 4      2      g                                            Stearic acid               2      g                                            Stearyl alcohol            1      g                                            Liquid paraffin            12.5   g                                            2-Ethylhexyl para-methoxycinnamate sold                                                                   2.5    g                                            under the name "PARSOL MCX" by the                                             company GIVAUDAN                                                               Glycerine                  3      g                                            Acrylic acid/C.sub.10 -C.sub.30 ethyl acrylate                                                            0.3    g                                            crosslinked copolymer sold under the name                                      "PEMULEN TR-1" by the company                                                  GOODRICH                                                                       Triethanolamine            0.4    g                                            Preserving agents qs                                                           Water qs                   100    g                                            EXAMPLE L: Conditioner                                                         Compound of Example 6      0.3    g                                            Distearyldimethylammonium chloride                                                                        2      g                                            Fragrance - dye qs                                                             Water qs                   100    g                                            pH adjusted to 5 with sodium hydroxide                                         EXAMPLE M: Shampoo                                                             Compound of Example 4      3      g                                            Alkyl (C.sub.9 /C.sub.10 /C.sub.11 - 20/40/40) (1.4)                                                      12     g AS                                         polyglucoside sold at a concentration of                                       50 g % of active substance by the company                                      HENKEL                                                                         Preserving agent, fragrance, dye qs                                            Water qs                   100    g                                            pH adjusted to 6 with hydrochloric acid.                                       A slightly opalescent composition is obtained.                                 EXAMPLE N: Deodorant stick                                                     Compound of Example 4      0.2    g                                            Sodium hydroxide           1      g                                            Stearic acid               5      g                                            Propylene glycol           50     g                                            2,4,4'-Trichloro-2-hydroxydiphenyl ether                                                                  0.3    g                                            sold under the name "IRGASAN DP 300" by                                        the company CIBA-GEIGY                                                         Water qs                   100    g                                            EXAMPLE O: Styling lotion                                                      Vinylpyrrolidone-vinyl acetage [sic]                                                                      10     g                                            (65/35) copolymer sold under tha name                                          "RESINE PVP/VA S 630 L" by the                                                 company GAF                                                                    Compound of Example 2      0.25   g                                            Poly(hydroxypropyl ether) prepared by                                                                     0.1    g                                            condensation, under alkaline catalysis, of                                     3.5 mol of glycidol with a mixture of alpha-                                   diols having 10 to 14 carbons                                                  Ethyl alcohol              45.2   g                                            Fragrance, dye, preserving agent qs                                            Demineralized water qs     100    g                                            Spontaneous pH of 4.9.                                                         An opalescent solution is obtained.                                            EXAMPLE P: Styling mousse                                                      An aerosol styling mousse having the                                           following composition is prepared:                                             Hydroxyethylcellulose diallyldimethyl-                                                                    1      g                                            ammonium chloride copolymer "CELQUAT                                           LOR" [lacuna] by the company                                                   NATIONAL STARCH                                                                Compound of Example 6      0.2    g                                            Ethyl alcohol              17.3   g                                            Oxyethylenated octylphenol containing                                                                     0.2    g                                            10 mol of ethylene oxide, sold under the name                                  "SCUROL O" by the company SFOS                                                 Fragrance, dye, preserving agent qs                                            Water qs                   100    g                                            90 g of the composition obtained are introduced                                into an aerosol container with plunger tube. The                               valve is attached and the receptacle is closed                                 hermetically, followed by introduction of 10 g                                 of a butane/isobutane/propane propellant                                       mixture (0.32 MPa (3.2 bar)).                                                  EXAMPLE Q                                                                      A reducing composition for the permanent                                       reshaping of the hair is prepared by mixing                                    the following ingredients:                                                     Reducing composition:                                                          Compound of Example 2      0.25   g                                            Oxyethylated octylphenol containing                                                                       2      g                                            10 mol of ethylene oxide, sold under the name                                  "SCUROL O" by the company SFOS                                                 Hot demineralized water    60     g                                            Thioglycolic acid          9      g                                            20% Aqueous ammonia qs     pH     8.2                                          Demineralized water qs     100    g                                            This composition is applied to wet hair which                                  has been wound beforehand on rollers. After                                    allowing the composition to act for 15 minutes,                                the hair is rinsed thoroughly with water and                                   the following composition is then applied:                                     Oxidizing composition:                                                         Hydrogen peroxide          1.5    g                                            Oxyethylenated sodium lauryl ether sulfate                                                                3.75   g                                            with 2 mol of ethylene oxide                                                   Citric acid                0.5    g                                            Sodium hydrogen phosphate  0.5    g                                            Fragrance                  0.3    g                                            Demineralized water qs     100    g                                            The oxidizing composition is allowed to act for                                about 15 minutes, then the rollers are removed                                 and the head of hair is rinsed thoroughly with                                 water. After drying under a hood, the hair has                                 beautiful curls.                                                               EXAMPLE R                                                                      A permanent reshaping of hair is performed                                     according to the same embodiment of Example                                    Q, using the following reducing composition:                                   Compound of Example 2      0.25   g                                            Oxyethylated octylphenol containing                                                                       2      g                                            10 mol of ethylene oxide, sold under the name                                  "SCUROL O" by the company SFOS                                                 Hot demineralized water    20     g                                            Glycerol thioglycolate (70% active                                                                        10     g                                            substance in glycerol)                                                         Triethanolmaine [sic] qs   pH     7                                            Demineralized water qs     100    g                                            The oxidizing composition is the same as that of                               Example Q.                                                                     EXAMPLE S: Tinted water-in-oil care cream                                      Alkyldimethicone copolyol sold under the                                                                  5.00   g                                            name "ABIL EM 90" by the company                                               GOLDSCHMIDT                                                                    Stearalkonium hectorite    2.00   g                                            Octyldodecanol             8.00   g                                            Decamethylcyclopentasiloxane                                                                              20.00  g                                            Fragrance qs                                                                   Preserving agent qs                                                            Glycerine                  3.00   g                                            Pigments                   7.00   g                                            Compound of Example 1      0.50   g                                            Sodium chloride            1.50   g                                            Demineralized water qs     100    g                                            EXAMPLE T: Tinted water-in-oil care cream                                      Magnesium aluminum silicate                                                                               0.50   g                                            Carboxymethylcellulose     0.15   g                                            Propylene glycol           5.00   g                                            Preserving agents qs                                                           Compound of Example 4      1.00   g                                            Lanolin alcohol            1.50   g                                            Glyceryl stearate          1.00   g                                            Steraric [sic] acid        2.50   g                                            Triethanolamine            1.50   g                                            Triglycerides of capric/caprylic acid                                                                     6.00   g                                            Polyisobutene              10.00  g                                            Nylon powder               3.00   g                                            Pigments                   10.00  g                                            Demineralized water qs     100    g                                            EXAMPLE U: Mascara                                                             Triethanolamine stearate   15.00  g                                            Paraffin                   3.00   g                                            Beeswax                    8.00   g                                            Compound of Example 1      0.50   g                                            Colophane                  2.00   g                                            Ozokerite                  10.00  g                                            Preserving agents qs                                                           Gum arabic                 0.60   g                                            Keratin hydrolysate        1.00   g                                            Pigments                   6.00   g                                            Demineralized water qs     100    g                                            EXAMPLE V: Treatment base for the nails:                                       Nitrocellulose             12.00  g                                            Toluenesulfonamide-formaldehyde resin                                                                     9.00   g                                            Camphor                    1.00   g                                            Dibutyl phthalate          6.05   g                                            Butyl acetate              24.00  g                                            Isopropyl acetate          6.00   g                                            Stearalkonium hectorite    1.00   g                                            Compound of Example 4      0.01   g                                            Citric acid                0.02   g                                            Toluene qs                 100    g                                            EXAMPLE W: Lipstick                                                            Butylhydroxytoluene        0.20   g                                            Liquid lanolin             17.50  g                                            Microscrystalline [sic] wax                                                                               15.00  g                                            Triglycerides of capric/caprylic acids                                                                    11.00  g                                            Oxtyl [sic] glyceryl behenate                                                                             11.00  g                                            Pigments                   3.00   g                                            Titanium mica              6.00   g                                            Fragrance                  0.50   g                                            Castor oil qs              100    g                                            EXAMPLE X: Lipstick                                                            Fragrance                  0.50   g                                            Triglycerides of capric/caprylic acids                                                                    9.10   g                                            Castor oil                 9.10   g                                            Butylhydroxytoluene        0.16   g                                            Liquid lanolin             12.70  g                                            Isopropyl lanolin          4.50   g                                            Compound of Example 1      0.50   g                                            Microcrystalline wax       11.00  g                                            Vinyl acetate/allyl stearate (65/35)                                                                      4.50   g                                            copolymer                                                                      Octyl glyceryl behenate    9.10   g                                            Pigments                   9.00   g                                            Sesame oil qs              100    g                                            EXAMPLE Y: Conditioner                                                         Distearyldimethylammonium chloride                                                                        2.00   g                                            Compound of Example 5      0.5    g                                            N-(Hydroxymethyl)-N-(1,3-dihydroxymethyl-                                                                 0.1    g                                            2,5-dioxo-4-imidazolidinyl)-N'-(hydroxy-                                       methyl)urea                                                                    Water qs                   100    g                                            Spontaneous pH: 4                                                              ______________________________________                                     

We claim:
 1. Compound, having the formula: ##STR9## in which R³ is a saturated linear C₂₂ -C₄₀ aliphatic radical, R⁴ is a hydrogen atom or a linear C₁ -C₆ alkyl radical and m is an integer from 1 to
 5. 2. The compound of claim 1, wherein R³ is a saturated linear C₂₂ -C₂₆ aliphatic radical.
 3. The compound of claim 1, wherein m is equal to
 4. 4. 1-(Docosyl-oxycarbonyl-methyl-amino)-1-deoxy-D-glucitol. 